Evidences of strong C-H····O bond in an o-carboranyl β-lactoside in solution

In this communication, the presence of a persistent intramolecular C-H⋯O bond in solution, has been evidenced by NMR spectroscopy and theoretical calculations. The molecules under study were o-carboranyl β-glycoside derivatives, in which, the donor group was the activated CH of the carboranyl residue and the acceptor atom was the glycosidic oxygen. The strength of the interaction and the geometry of the atoms involved were determined by ab initio calculations.